At the Oregon City shop You can leave your Hat On, every purchase comes with a chocolate and plenty of sweet compliments.

“Doesn’t she look beautiful? And so young,” owner Sandra Gillman says as she places a hat on a customer.

She opened about three years ago, ordering hundreds of hats from around the world.

“Most customers spend between $30 and $80 dollars,” Sandra says. “I like to know where they’re going, what they’ll be wearing, but most of all I know they’ve found the right one if they feel like dancing.”

With the Kentucky Derby coming up on May 3, Sandra’s business is at a record-setting pace.

“We’ve had a few groups come in for parties, women celebrating as they select their hats for race day,” Sandra explains.

It’s a colorful contrast to Sandra’s former job working on criminal defense mitigation.

“I spent a lot of time in prisons, looking at autopsy and police reports. This is just the opposite,” she says. “I love to see the way a woman walks to the mirror when she puts a hat on. She feels like a lady.”

Selling Derby hats is fun, but her favorite customers are those in need of a hat because they’ve lost their hair to chemotherapy.

“The worst part was finding out I had cervical cancer,” said customer Dale Paulus. “But for whatever reason the hair part has been really hard, too, so finding this place is a lifesaver.”

As with her other customers, Sandra gives Dale advice on several styles, always reminding her that the embellishment on any hat goes over the temple.

Within 20 minutes, Dale is beaming with her selections,

“Wearing this makes me feel like I can look straight ahead when I walk outside now instead of looking down,” she says, tears welling in her eyes.

Dale leaves with three hats and three chocolates, another customer satisfied by the sweetness of the woman known as the “Hat Lady”

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Tarri Y-P : A recent Customer

From the moment I first entered the store I was in ❤️love. Hats hatseverywhere! ⬆️➡️⬇️⬅️ I bought two hats that day and have returned several times to add to my collection. I wasn't even a "hat person" when I walked in! So come on down to Oregon City and check it out. It's always a good day to buy a hat!